title: Synthesis of fluorinated purine and 1-deazapurine glycosides as potential inhibitors of adenosine deaminase.
abstract: The synthesis of 2- and 6-trifluoromethylated purines and 1-deazapurines was performed by formal [3 + 3]-cyclization reactions of 5-aminoimidazoles with a set of trifluoromethyl-substituted 1,3-CCC- and 1,3-CNC-dielectrophiles. The corresponding fluorinated nucleosides were synthesized by glycosylation of 9-unsubstituted purines and 1-deazapurines with peracetylated β-ribose, β-glucose, and rhamnose and subsequent deprotection. These scaffolds can be considered as potential inhibitors of adenosine deaminase (ADA) and inosine monophosphate dehydrogenase (IMPDH) enzymes.
authors.affiliation: Institut für Chemie der Universität Rostock, Albert-Einstein-Strasse 3a, D-18059 Rostock, Germany. viktor.iaroshenko@uni-rostock.de
authors.forename: Viktor O
authors.initials: VO
authors.lastname: Iaroshenko
authors.forename: Dmytro
authors.initials: D
authors.lastname: Ostrovskyi
authors.forename: Andranik
authors.initials: A
authors.lastname: Petrosyan
authors.forename: Satenik
authors.initials: S
authors.lastname: Mkrtchyan
authors.forename: Alexander
authors.initials: A
authors.lastname: Villinger
authors.forename: Peter
authors.initials: P
authors.lastname: Langer
mesh_terms: D000243:Adenosine Deaminase / Q000378:metabolism; D058892:Adenosine Deaminase Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology; D003500:Cyclization; D006027:Glycosides / Q000138:chemical synthesis* / Q000494:pharmacology; D006031:Glycosylation; D054879:Halogenation; D006801:Humans; D007168:IMP Dehydrogenase / Q000037:antagonists & inhibitors; D007093:Imidazoles / Q000737:chemistry; D018716:Molecular Mimicry; D009005:Monosaccharides / Q000737:chemistry; D011687:Purines / Q000138:chemical synthesis* / Q000494:pharmacology
chemical_list: D058892:Adenosine Deaminase Inhibitors; D006027:Glycosides; D007093:Imidazoles; D009005:Monosaccharides; D011687:Purines; C064191:1H-imidazo(4,5-b)pyridine; C098330:4-aminoimidazole; D007168:IMP Dehydrogenase; C488211:IMPDH1 protein, human; D000243:Adenosine Deaminase